NO128608B - - Google Patents
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- Publication number
- NO128608B NO128608B NO01825/69A NO182569A NO128608B NO 128608 B NO128608 B NO 128608B NO 01825/69 A NO01825/69 A NO 01825/69A NO 182569 A NO182569 A NO 182569A NO 128608 B NO128608 B NO 128608B
- Authority
- NO
- Norway
- Prior art keywords
- steroid
- pregnan
- oxazoline
- heated
- carbon atoms
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 150000003128 pregnanes Chemical class 0.000 claims description 5
- 150000003431 steroids Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 3
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- -1 steroid oxazolines Chemical class 0.000 description 3
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 150000002918 oxazolines Chemical class 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0057—Nitrogen and oxygen
- C07J71/0068—Nitrogen and oxygen at position 16(17)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0011—Unsubstituted amino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO366473A NO131600C (nl) | 1968-05-03 | 1973-09-19 | |
| NO366373A NO131133C (nl) | 1968-05-03 | 1973-09-19 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1602968 | 1968-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128608B true NO128608B (nl) | 1973-12-17 |
Family
ID=11148457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01825/69A NO128608B (nl) | 1968-05-03 | 1969-05-02 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3631033A (nl) |
| AT (2) | AT300218B (nl) |
| BE (1) | BE731718A (nl) |
| BR (1) | BR6908511D0 (nl) |
| CH (1) | CH511823A (nl) |
| DE (1) | DE1921778A1 (nl) |
| DK (2) | DK124680B (nl) |
| ES (2) | ES366738A1 (nl) |
| FI (3) | FI46374C (nl) |
| FR (1) | FR2007756B1 (nl) |
| GB (1) | GB1254487A (nl) |
| IL (1) | IL31997A (nl) |
| LU (1) | LU58451A1 (nl) |
| NL (2) | NL6906149A (nl) |
| NO (1) | NO128608B (nl) |
| SE (4) | SE363098B (nl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7107998A (nl) * | 1970-07-09 | 1972-01-11 | ||
| IT1134455B (it) * | 1980-11-26 | 1986-08-13 | Lepetit Spa | Procedimento per la preparazione di derivati 16alfa-idrossi-17alfa-aminopregnanici |
| US20030083231A1 (en) * | 1998-11-24 | 2003-05-01 | Ahlem Clarence N. | Blood cell deficiency treatment method |
| CA2496867A1 (en) * | 2002-08-28 | 2004-03-11 | Hollis-Eden Pharmaceuticals, Inc. | Therapeutic treatment methods |
| US20050101581A1 (en) * | 2002-08-28 | 2005-05-12 | Reading Christopher L. | Therapeutic treatment methods 2 |
| CN102482318B (zh) * | 2009-09-11 | 2015-11-25 | 奇斯药制品公司 | 异噁唑烷衍生物 |
| EP2716648B1 (en) * | 2011-03-15 | 2017-06-14 | CHIESI FARMACEUTICI S.p.A. | Isoxazolidine derivatives |
| KR20140039161A (ko) | 2011-03-15 | 2014-04-01 | 키에시 파르마슈티시 엣스. 피. 에이. | 이소옥사졸리딘 유도체 |
| US9155747B2 (en) * | 2012-09-13 | 2015-10-13 | Chiesi Farmaceutici S.P.A. | Isoxazolidine derivatives |
-
1969
- 1969-04-11 IL IL31997A patent/IL31997A/xx unknown
- 1969-04-18 LU LU58451D patent/LU58451A1/xx unknown
- 1969-04-18 BE BE731718D patent/BE731718A/xx unknown
- 1969-04-21 NL NL6906149A patent/NL6906149A/xx unknown
- 1969-04-24 DK DK224769AA patent/DK124680B/da unknown
- 1969-04-29 DE DE19691921778 patent/DE1921778A1/de not_active Withdrawn
- 1969-04-30 FR FR6913817A patent/FR2007756B1/fr not_active Expired
- 1969-05-01 US US821149A patent/US3631033A/en not_active Expired - Lifetime
- 1969-05-02 FI FI691290A patent/FI46374C/fi active
- 1969-05-02 SE SE06253/69A patent/SE363098B/xx unknown
- 1969-05-02 CH CH673969A patent/CH511823A/fr not_active IP Right Cessation
- 1969-05-02 SE SE7203865A patent/SE373131B/xx unknown
- 1969-05-02 SE SE7203864A patent/SE373578B/xx unknown
- 1969-05-02 NO NO01825/69A patent/NO128608B/no unknown
- 1969-05-02 GB GB22523/69A patent/GB1254487A/en not_active Expired
- 1969-05-02 AT AT758070A patent/AT300218B/de not_active IP Right Cessation
- 1969-05-02 BR BR208511/69A patent/BR6908511D0/pt unknown
- 1969-05-02 SE SE7203863A patent/SE378250B/xx unknown
- 1969-05-02 AT AT426169A patent/AT291450B/de not_active IP Right Cessation
- 1969-05-03 ES ES366738A patent/ES366738A1/es not_active Expired
- 1969-09-29 ES ES371991A patent/ES371991A1/es not_active Expired
-
1970
- 1970-11-10 DK DK569770AA patent/DK128352B/da unknown
-
1971
- 1971-12-29 FI FI713714A patent/FI46376C/fi active
- 1971-12-29 FI FI713715A patent/FI46377C/fi active
-
1977
- 1977-09-02 NL NL7709675A patent/NL7709675A/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2007756A1 (nl) | 1970-01-09 |
| NL7709675A (nl) | 1977-12-30 |
| FI46374C (fi) | 1973-03-12 |
| BE731718A (nl) | 1969-10-01 |
| DK128352B (da) | 1974-04-16 |
| FI46376B (nl) | 1972-11-30 |
| GB1254487A (en) | 1971-11-24 |
| BR6908511D0 (pt) | 1973-02-08 |
| SE373578B (sv) | 1975-02-10 |
| US3631033A (en) | 1971-12-28 |
| DE1965963A1 (de) | 1970-12-23 |
| NL6906149A (nl) | 1969-11-05 |
| AT291450B (de) | 1971-07-12 |
| IL31997A (en) | 1974-03-14 |
| SE373131B (nl) | 1975-01-27 |
| FR2007756B1 (nl) | 1975-10-10 |
| ES371991A1 (es) | 1971-12-01 |
| DE1965963B2 (de) | 1973-02-08 |
| FI46374B (nl) | 1972-11-30 |
| ES366738A1 (es) | 1971-03-16 |
| FI46377B (nl) | 1972-11-30 |
| CH511823A (fr) | 1971-08-31 |
| FI46377C (fi) | 1973-03-12 |
| FI46376C (fi) | 1973-03-12 |
| LU58451A1 (nl) | 1969-07-21 |
| SE363098B (nl) | 1974-01-07 |
| IL31997A0 (en) | 1969-06-25 |
| DE1921778A1 (de) | 1969-11-20 |
| SE378250B (nl) | 1975-08-25 |
| DK124680B (da) | 1972-11-13 |
| AT300218B (de) | 1972-07-25 |
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